Phosphorus oxychloride → HCID 86640732, 화합물

HRID 529425노트

반응식

HRID 529425 반응식
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[C:8]([F:14])=[N+:9]([O-])[CH:10]=[CH:11][CH:12]=2)=[C:4]([C:17](=[O:23])[N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH:3]=1.P(Cl)(Cl)([Cl:26])=O>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[C:8]([F:14])=[N:9][C:10]([Cl:26])=[CH:11][CH:12]=2)=[C:4]([CH:3]=1)[C:17]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:23]

참가 물질

5

반응물 2

HCID 24813Phosphorus oxychlorideHCID 667281373-(4-Bromo-2-(diethylcarbamoyl)phenoxy)-2-fluoropyridine 1-oxide

생성물 1

HCID 86640732HCID 86640732, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-(4-bromo-2-(diethylcarbamoyl)phenoxy)-2-fluoropyridine 1-oxide (420 mg, 1.096 mmol) in 15 mL of DCM was added dropwise phosphorus oxychloride (301 μL, 3.29 mmol) followed by 2 drops of DMF. After stirring at rt for 1 h, the reaction was quenched with sat. NaHCO3, extracted into EtOAc, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude was purified by column chromatography (DCM to DCM/EtOAc gradient beginning from 10:1 to 5:1 to 3:1) gave 5-bromo-2-(6-chloro-2-fluoropyridin-3-yloxy)-N,N-diethylbenzamide as a colorless gum.

후처리

  1. customthe reaction was quenched with sat. NaHCO3
  2. extractionextracted into EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by column chromatography (DCM to DCM/EtOAc gradient beginning from 10:1 to 5:1 to 3:1)

출처 및 근거

ORD 기록
ord-a8232490459e4e408e54954e5f090fb4
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346827B2

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